ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate | 790223-53-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate
• 英文别名: ethyl (4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-5-phenylpentanoate
• CAS: 790223-53-9
• 化学式: C₁₈H₂₇NO₄
• 分子量: 321.417
• InChiKey: VTNMBJFMLIWRJC-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以91%的产率得到(S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoic acid
  参考文献：
  名称：

  [EN] NK-2 ANTAGONIST BASIC LINEAR COMPOUNDS AND FORMULATIONS CONTAINING THEM
  [FR] COMPOSES LINEAIRES DE BASE D'ANTAGONISTES DE NK-2 ET FORMULATIONS LES CONTENANT

  摘要：

  本发明描述了具有公式（I）的化合物，具有线性结构基本性质，可用作NK-2拮抗剂；还描述了含有这些化合物的药物组合物以及它们的制备过程。

  公开号：

  WO2004094412A1
• 作为产物：
  描述：

  N-Boc-D-苯丙氨醛 在 palladium on activated charcoal 、 氢气 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 ethyl (S)-4-((tert-butoxycarbonyl)amino)-5-phenylpentanoate
  参考文献：
  名称：

  Consequence of Hapten Stereochemistry: An Efficacious Methamphetamine Vaccine

  摘要：

  Recent trends in methamphetamine (METH) misuse and overdose suggest society is inadvertently overlooking a brewing METH crisis. In the past decade, psychostimulant-related lethal overdoses and hospitalizations have skyrocketed 127 and 245%, respectively. Unlike the opioid crisis, no pharmaceutical interventions are available for treating METH use disorder or reversing overdose. Herein, we report the first active vaccine that offers protection from lethal (+)-METH challenge in male Swiss Webster mice. This vaccine formulation of (S)MLMH-TT adjuvanted with CpG ODN 1826 + alum successfully raised anti-METH antibodies in high titers, reduced (+)-METH distribution to the brain, and lowered (+)-METH-associated stereotypies in a hyperlocomotion assay. A comparison of enantiomeric haptens and the racemate elucidated the importance of employing (S)-stereochemistry in METH hapten design for optimal protection.

  DOI：

  10.1021/jacs.9b07294

文献信息

• [EN] NK-2 ANTAGONIST BASIC LINEAR COMPOUNDS AND FORMULATIONS CONTAINING THEM<br/>[FR] COMPOSES LINEAIRES DE BASE D'ANTAGONISTES DE NK-2 ET FORMULATIONS LES CONTENANT
  申请人：MENARINI RICERCHE SPA

  公开号：WO2004094412A1

  公开（公告）日：2004-11-04

  The present invention describes compounds with formula (I) having linear structure basic properties useful as NK-2 antagonists; pharmaceutical compositions containing said compounds are also described and processes for their preparation.

  本发明描述了具有公式（I）的化合物，具有线性结构基本性质，可用作NK-2拮抗剂；还描述了含有这些化合物的药物组合物以及它们的制备过程。
• Nk-2 antagonist basic linear compounds and formulations containing them
  申请人：Fattori Daniela

  公开号：US20060223814A1

  公开（公告）日：2006-10-05

  The present invention describes compounds with formula (I) having linear structure basic properties useful as NK-2 antagonists; pharmaceutical compositions containing said compounds are also described and processes for their preparation.

  本发明描述了具有公式(I)的化合物，其具有线性结构基本性质，可用作NK-2拮抗剂；还描述了含有所述化合物的药物组合物以及其制备过程。
• Practical Approach for Asymmetric Hydroxyamination of Aldehydes with <i>in Situ</i> Generated Nitrosocarbonyl Compounds: Application to One-Pot Synthesis of Chiral Allylamines
  作者：Taichi Kano、Fumitaka Shirozu、Keiji Maruoka

  DOI：10.1021/ol5000742

  日期：2014.3.7

  The highly regio- and enantioselective hydroxyamination of aldehydes with in situ generated nitrosocarbonyl compounds from a hydroxamic acid derivative was realized by simple and readily available chiral amine catalysts. The resulting hydroxyamination products were readily converted to the corresponding chiral 1,2-aminoalcohol or allylamine derivatives in one pot.
• NK-2 ANTAGONIST BASIC LINEAR COMPOUNDS AND FORMULATIONS CONTAINING THEM
  申请人：Menarini Ricerche S.p.A.

  公开号：EP1620432A1

  公开（公告）日：2006-02-01
• Structure−Activity Relationships of 6-Methyl-benzo[<i>b</i>]thiophene-2-carboxylic Acid (1-{(<i>S</i>)-1-Benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl}cyclopentyl)amide, Potent Antagonist of the Neurokinin-2 Receptor
  作者：Daniela Fattori、Marina Porcelloni、Piero D’Andrea、Rose-Marie Catalioto、Alessandro Ettorre、Sandro Giuliani、Elena Marastoni、Sandro Mauro、Stefania Meini、Cristina Rossi、Maria Altamura、Carlo A. Maggi

  DOI：10.1021/jm100176s

  日期：2010.5.27

  As part of a project aimed at the identification of a series of small, orally available antagonists for the hNK(2) receptor, starting from one of our capped dipeptide libraries, we succeeded in the chemical optimization of the first identified leads, finally producing a class of molecules with significant activity in our animal model after iv administration. We herein report the results of further chemical modifications made to reduce the overall peptide character of this series and the consequent improvement of their in vivo antagonist activity. The present work identified 6-methylbenzo[b]thiophene-2-carboxylic acid (1-(S)-1-benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl}cyclopentyl)amide (10i), endowed with subnanomolar potency in all the in vitro tests and being highly potent and of long duration upon in vivo testing after both iv and id dosing.